US2023104690A1PendingUtilityA1
MATRIX METALLOPROTEINASE INHIBITORS (MMPIs)
Est. expiryJun 29, 2040(~13.9 yrs left)· nominal 20-yr term from priority
A61P 35/00C07K 5/06043A61K 38/55
47
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Claims
Abstract
Relates to a compound of Formula I a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof. Also, relates to a compound of Formula II a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof. The compounds can be a matrix metalloproteinase (MMP) inhibitor. The compounds can also treat a matrix metalloproteinase mediated condition such as cancer.
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A compound of Formula I:
a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof;
wherein:
R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , and R 12 , are each independently selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic; and
R 13 is selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group,
substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
2 . A compound of Formula II:
a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof; wherein:
R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 , are each independently selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic; and
R 13 is selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
3 . The compound according to claim 1 or 2 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted carbocyclic group, or a substituted or unsubstituted heterocyclic group.
4 . The compound according to claim 3 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted hydroxyalkyl group, a substituted or unsubstituted cyanoalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted C 1 -C 6 alkylcarbonyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkylcycloalkyl group, a substituted or unsubstituted alkylcycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkylheterocycloalkyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkylheterocycloalkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkylaryl group, or a substituted or unsubstituted alkylheteroaryl group.
5 . The compound according to claim 4 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H or a substituted or unsubstituted alkyl group.
6 . The compound according to claim 5 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group.
7 . The compound according to claim 6 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H or a substituted or unsubstituted H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3 dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
8 . The compound according to claim 7 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
9 . The compound according to claim 8 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
10 . The compound according to claim 1 or 2 , wherein R, R 1 , R 2 , R 3 , R 4 , and R 5 are each H and R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H or a substituted or unsubstituted alkyl group.
11 . The compound according to claim 10 , wherein R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group.
12 . The compound according to claim 11 , wherein R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H or a substituted or unsubstituted methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2 methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
13 . The compound according to claim 12 , wherein R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
14 . The compound according to claim 13 , wherein R 6a , R 6b , R 7 , R 8a , R 8b , R 9 , R 10a , R 10b , R 11a , R 11b , and R 12 are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
15 . The compound according to claim 1 or 2 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 9 , R 11a , R 11b , and R 12 are each H and R 8a , R 8b , R 10a , and R 10b are each independently selected from H or a substituted or unsubstituted alkyl group.
16 . The compound according to claim 15 , wherein R 8a , R 8b , R 10a , and R 10b are each independently selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group.
17 . The compound according to claim 16 , wherein R 8a , R 8b , R 10a , and R 10b are each independently selected from H or a substituted or unsubstituted methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
18 . The compound according to claim 17 , wherein R 8a , R 8b , R 10a , and R 10b are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3 methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
19 . The compound according to claim 18 , wherein R 8a , R 8b , R 10a , and R 10b are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
20 . The compound according to claim 1 or 2 , wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 9 , R 10a , R 11a , R 11b , and R 12 are each H and R 8b and R 10b are each independently selected from H or a substituted or unsubstituted alkyl group.
21 . The compound according to claim 20 , wherein R 8b and R 10b are each independently selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group.
22 . The compound according to claim 21 , wherein R 8b and R 10b are each independently selected from H or a substituted or unsubstituted methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
23 . The compound according to claim 22 , wherein R 8b and R 10b are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3 methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
24 . The compound according to claim 23 , wherein R 8b and R 10b are each independently selected from H, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
25 . The compound according to claim 23 , wherein R 8b is selected from methyl or ethyl, and R 10b is selected from methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
26 . The compound according to claim 23 , wherein R 8b is methyl and R 10b is selected from 1-butyl, i-butyl, sec-butyl, or t-butyl.
27 . The compound according to claim 23 , wherein R 8b is selected from methyl, and R 10b is i-butyl.
28 . The compound according to any one of claims 1 to 27 , wherein R 13 is selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
29 . The compound according to claim 28 , wherein R 13 is selected from H, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted carbocyclic group, or a substituted or unsubstituted heterocyclic group.
30 . The compound according to claim 29 , wherein R 13 is selected from H, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted hydroxyalkyl group, a substituted or unsubstituted aminoalkyl group, a substituted or unsubstituted thioalkyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted carboxy group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cyanoalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted C 1 -C 6 alkylcarbonyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted alkylcycloalkyl, a substituted or unsubstituted alkylcycloalkenyl, a substituted or unsubstituted heterocycloalkyl, a substituted or unsubstituted alkylheterocycloalkyl, a substituted or unsubstituted heterocycloalkenyl, a substituted or unsubstituted alkylheterocycloalkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl.
31 . The compound according to claim 28 , wherein R 13 is selected from H, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, —NR 14 R 15 , —CR 16 R 17 R 18 , —C(O)NR 19 R 20 , halo group, —S(O)R 21 , —SO 2 R 22 , —R 23 S(O)R 24 , —R 25 SO 2 R 26 , —R 27 SR 28 , —R 27 S—C(O)R 28 , —SR 29 , —S—C(O)R 30 , —C(O)SR 31 , —N(R 32 )C(O)R 33 , —C(O)R 34 , —C(O)OR 35 , or —OR 36 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
32 . The compound according to claim 31 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted hydroxyalkyl group, a substituted or unsubstituted cyanoalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted C 1 -C 6 alkylcarbonyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkylcycloalkyl group, a substituted or unsubstituted alkylcycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkylheterocycloalkyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkylheterocycloalkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
33 . The compound according to claim 32 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group.
34 . The compound according to claim 33 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, or a substituted or unsubstituted C 1 -C 6 alkyl group.
35 . The compound according to claim 34 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2 methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
36 . The compound according to claim 35 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a thiol group, an amino group, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
37 . The compound according to claim 36 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a thiol group, an amino group, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
38 . The compound according to claim 28 , wherein R 13 is selected from —NR 14 R 15 , —CR 16 R 17 R 18 , —R 27 SR 28 , —R 27 S—C(O)R 28 , —C(O)SR 31 , —N(R 32 )C(O)R 33 , —C (O)R 34 , —C(O)OR 35 , or —OR 36 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, carboxylic acid group, phosphate group, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, nitro group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
39 . The compound according to claim 38 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted hydroxyalkyl group, a substituted or unsubstituted cyanoalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted C 1 -C 6 alkylcarbonyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkylcycloalkyl group, a substituted or unsubstituted alkylcycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted alkylheterocycloalkyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted alkylheterocycloalkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
40 . The compound according to claim 39 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group.
41 . The compound according to claim 40 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, or a substituted or unsubstituted C 1 -C 6 alkyl group.
42 . The compound according to claim 41 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted methyl, ethyl, 1-propyl, i propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
43 . The compound according to claim 42 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a thiol group, an amino group, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, t-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2 methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, or hexyl.
44 . The compound according to claim 43 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a thiol group, an amino group, methyl, ethyl, 1-propyl, i-propyl, 1-butyl, i-butyl, sec-butyl, or t-butyl.
45 . The compound according to any one of claims 38 to 44 , wherein R 13 is selected from hydroxyl group, —NR 14 R 15 , or —CR 16 R 17 R 18 , wherein R 14 , R 15 , R 16 R 17 , and R 18 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
46 . The compound according to claim 45 , wherein R 14 , R 15 , R 16 R 17 , R 18 , R 27 , R 28 , R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 are each independently selected from H, halo group, hydroxyl group, a thiol group, an amino group, a substituted or unsubstituted alkyl group, or —S—C(O)R 37 , wherein R 37 is selected from H or a substituted or unsubstituted alkyl group.
47 . The compound according to claim 45 or 46 , wherein R 13 is a hydroxyl group.
48 . The compound according to claim 45 or 46 , wherein R 13 is —NR 14 R 15 , wherein R 14 and R 15 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
49 . The compound according to claim 48 , wherein R 14 and R 15 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, or a substituted or unsubstituted alkyl group.
50 . The compound according to claim 48 , wherein R 14 and R 15 are each independently selected from H, hydroxyl group, a thiol group, or a substituted or unsubstituted C 1 -C 6 alkyl group.
51 . The compound according to claim 48 , wherein R 14 is H or C 1 -C 6 alkyl group and R 15 is selected from H, hydroxyl group, or a thiol group.
52 . The compound according to claim 45 or 46 , wherein R 13 is —CR 16 R 17 R 18 , wherein R 16 , R 17 , and R 18 are each independently selected from H, halo group, hydroxyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amino group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic.
53 . The compound according to claim 52 , wherein R 16 , R 17 , and R 18 are each independently selected from H, halo group, hydroxyl group, a thiol group, an amino group, a substituted or unsubstituted alkyl group, or —S—C(O)R 37 , wherein R 37 is selected from H or a substituted or unsubstituted alkyl group.
54 . The compound according to claim 53 , wherein R 16 and R 17 are each independently selected from H or a substituted or unsubstituted alkyl group and R 18 is selected from a halo group, hydroxyl group, a thiol group, an amino group, a substituted or unsubstituted alkyl group, or —S—C(O)R 37 , wherein R 37 is selected from H or a substituted or unsubstituted alkyl group.
55 . The compound according to claim 53 , wherein R 16 and R 17 are each independently selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group and R 18 is selected from a halo group, hydroxyl group, a thiol group, an amino group, a substituted or unsubstituted C 1 -C 6 alkyl group, or —S—C(O)R 37 , wherein R 37 is selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group.
56 . The compound according to claim 53 , wherein R 16 and R 17 are each independently selected from H and R 18 is selected from a halo group, hydroxyl group, a thiol group, or —S—C(O)R 37 , wherein R 37 is selected from H or a substituted or unsubstituted C 1 -C 6 alkyl group.
57 . The compound according to claim any one of claims 1 to 56 , wherein the compound of Formula I includes at least one compound selected from:
a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof.
58 . The compound according to any one of claims 1 to 57 , wherein the compound of Formula I includes at least one compound selected from:
a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof.
59 . The compound according to claim any one of claims 1 to 57 , wherein the compound of Formula II includes at least one compound selected from:
a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof.
60 . The compound according to any one of claims 1 to 57 , wherein the compound of Formula II includes at least one compound selected from:
a salt, hydrate, solvate, tautomer, enantiomer, racemate, diastereomer, or combination thereof.
61 . The compound according to any one of claims 1 to 57 , wherein the compound has an S configuration at the α-carbon with R 7 and an S configuration at the α-carbon with R 10a and R 10b .
62 . The compound according to any one of claims 1 to 61 , wherein the compound is a matrix metalloproteinase (MMP) inhibitor.
63 . The compound according to claim 62 , wherein the matrix metalloproteinase is MMP-3, MMP-8, and/or MMP-13.
64 . The compound according to claim 62 , wherein the matrix metalloproteinase is MMP-3.
65 . The compound according to any one of claims 62 to 64 , wherein R 13 —SO 2 NR 12 — of Formula I and/or Formula II bidentately ligates to the Zn 2+ ion of a matrix metalloproteinase (MMP) and/or is capable of forming a hydrogen bond to Glu202 of the matrix metalloproteinase (MMP).
66 . The compound according to any one of claims 1 to 65 for the treatment of a matrix metalloproteinase mediated condition.
67 . The compound according to claim 66 , wherein the matrix metalloproteinase mediated condition is selected from cancer, angiogenesis, cardiovascular disease, neurological disease, inflammation, eye disease, autoimmune disease, for regulating contraception, or other conditions that are affected by the regulation of MMPs.
68 . The compound of claim 67 , wherein the cancer is selected from pancreatic cancer, gastric cancer, lung cancer, colorectal cancer, prostate cancer, cervical cancer, ovarian cancer, cancer of CNS, renal cell cancer, basal cell cancer, breast cancer, bone cancer, brain cancer, lymphoma, leukemia, melanoma, myeloma, leukemia, or other hematological cancers.
69 . The compound according to claim 68 , wherein the cancer is selected from brain cancer, breast cancer, acute leukemia, chronic leukemia, colorectal cancer, or lung cancer.
70 . The compound according to claim 68 or 69 , wherein the cancer is GBM.
71 . The compound according to any one of claims 68 to 70 , wherein the cancer is a carcinoma.
72 . The compound according to claim 71 , wherein the carcinoma is selected from small cell carcinomas, cervical carcinomas, glioma, astrocytoma, prostate carcinomas, ovarian carcinomas, melanoma, breast carcinomas, brain carcinomas, or colorectal carcinomas.
73 . The compound according to any one of claims 1 to 72 in combination with radiation therapy.
74 . A pharmaceutical composition comprising the compound according to any one of claims 1 to 73 and at least one pharmaceutically acceptable carrier and/or diluent.
75 . The composition according to claim 74 further comprising an anti-cancer agent.
76 . A method for the treatment of a matrix metalloproteinase mediated condition in a mammal, comprising administering to the mammal a therapeutically effective amount of the compound according to any one of claims 1 to 65 or the composition of claim 74 or 75 .
77 . The method according to claim 76 , wherein the matrix metalloproteinase mediated condition is selected from cancer, angiogenesis, cardiovascular disease, neurological disease, inflammation, eye disease, autoimmune disease, for regulating contraception, or other conditions that are affected by the regulation of MMPs.
78 . The method of claim 77 , wherein the cancer is selected from pancreatic cancer, gastric cancer, lung cancer, colorectal cancer, prostate cancer, cervical cancer, ovarian cancer, cancer of CNS, renal cell cancer, basal cell cancer, breast cancer, bone cancer, brain cancer, lymphoma, leukemia, melanoma, myeloma, leukemia, or other hematological cancers.
79 . The method according to claim 78 , wherein the cancer is selected from brain cancer, breast cancer, acute leukemia, chronic leukemia, colorectal cancer, or lung cancer.
80 . The method according to claim 78 or 79 , wherein the cancer is GBM.
81 . The method according to any one of claims 78 to 80 , wherein the cancer is a carcinoma.
82 . The method according to claim 81 , wherein the carcinoma is selected from small cell carcinomas, cervical carcinomas, glioma, astrocytoma, prostate carcinomas, ovarian carcinomas, melanoma, breast carcinomas, brain carcinomas, or colorectal carcinomas.
83 . The method according to any one of claims 76 to 82 in combination with radiation therapy.
84 . The method according to any one of claims 76 to 83 , wherein the compound or composition is administered orally and/or parenterally.
85 . The method according to any one of claims 76 to 84 , wherein the mammal is a human.
86 . Use of a therapeutically effective amount of the compound according to any one of claims 1 to 65 or the composition of claim 74 or 75 for the treatment of a matrix metalloproteinase mediated condition in a mammal.
87 . The use according to claim 86 , wherein the matrix metalloproteinase mediated condition is selected from cancer, angiogenesis, cardiovascular disease, neurological disease, inflammation, eye disease, autoimmune disease, for regulating contraception, or other conditions that are affected by the regulation of MMPs.
88 . The use of claim 87 , wherein the cancer is selected from pancreatic cancer, gastric cancer, lung cancer, colorectal cancer, prostate cancer, cervical cancer, ovarian cancer, cancer of CNS, renal cell cancer, basal cell cancer, breast cancer, bone cancer, brain cancer, lymphoma, leukemia, melanoma, myeloma, leukemia, or other hematological cancers.
89 . The use according to claim 88 , wherein the cancer is selected from brain cancer, breast cancer, acute leukemia, chronic leukemia, colorectal cancer, or lung cancer.
90 . The use according to claim 88 or 89 , wherein the cancer is GBM.
91 . The use according to any one of claims 88 to 90 , wherein the cancer is a carcinoma.
92 . The use according to claim 91 , wherein the carcinoma is selected from small cell carcinomas, cervical carcinomas, glioma, astrocytoma, prostate carcinomas, ovarian carcinomas, melanoma, breast carcinomas, brain carcinomas, or colorectal carcinomas.
93 . The use according to any one of claims 86 to 92 in combination with radiation therapy.
94 . The use according to any one of claims 86 to 93 , wherein the compound or composition is administered orally and/or parenterally.
95 . The use according to any one of claims 86 to 94 , wherein the mammal is a human.Join the waitlist — get patent alerts
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